(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(5-methyl-2H-1,2,3,4-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid

• ChemBase ID: 163938
• Molecular Formular: C16H17N9O5S2
• Molecular Mass: 479.49348
• Monoisotopic Mass: 479.07940669
• SMILES: [C@H]1(C(=O)N2[C@@H]1SC=C(C2C(=O)O)Cn1nnc(n1)C)NC(=O)/C(=N\OC)/c1csc(n1)N
• Canonical SMILES: CO/N=C(\C(=O)N[C@@H]1C(=O)N2[C@@H]1SC=C(C2C(=O)O)Cn1nnc(n1)C)/c1csc(n1)N
• InChI: InChI=1S/C16H17N9O5S2/c1-6-20-23-24(21-6)3-7-4-31-14-10(13(27)25(14)11(7)15(28)29)19-12(26)9(22-30-2)8-5-32-16(17)18-8/h4-5,10-11,14H,3H2,1-2H3,(H2,17,18)(H,19,26)(H,28,29)/b22-9-/t10-,11?,14-/m1/s1
• InChIKey: RGVZHTDOHDQKKK-QIQDODJKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(5-methyl-2H-1,2,3,4-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(5-methyl-1,2,3,4-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid
• Synonyms: (6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[(5-methyl-2H-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic Acid; T 2525A; Δ2-Cefteram

Database IDs

• CAS Number: 104691-34-1
• PubChem SID: 162258073
• PubChem CID: 9982557

CALCULATED PROPERTIES

• Acid pKa: 2.676449
• H Acceptors: 11
• H Donor: 3
• LogD (pH = 5.5): -3.0611088
• LogD (pH = 7.4): -3.9401045
• Log P: -1.95096
• Molar Refractivity: 124.2614 cm^3
• Polarizability: 42.073395 Å^3
• Polar Surface Area: 190.81 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C244280

Cefteram metabolite.

REFERENCES

• Shimada, J., et al.: Jap. J. Antibio., 39, 2701 (1986)
• Saikawa, I., et al.: Chemother., 34, 158 (1986)